1. Field of the Invention
The present invention relates to N-substituted phenylcarbamic acid derivatives represented by the following general formula (I), a process for production thereof, agricultural and horticultural fungicides, intermediate of the derivatives, and a process for production of the intermediates: ##STR2## wherein R.sup.1 is a hydrogen atom, a (C.sub.1-6)alkyl group, a halo(C.sub.1-6)alkyl group, a (C.sub.1-6)alkoxy(C.sub.1-6)alkyl group, a (C.sub.2-6)alkenyl group, a (C.sub.2-6)alkynyl group or a halo(C.sub.1-6)alkoxy(C.sub.1-6)alkyl group, R.sup.2 is a hydrogen atom, a (C.sub.1-6)alkyl group, a halo(C.sub.1-6)alkyl group, a (C.sub.1-6)alkoxy(C.sub.1-6)alkyl group, a (C.sub.2-6)alkenyl group, a (C.sub.2-6)alkynyl group, a halo(C.sub.1-6)alkoxy(C.sub.1-6)alkyl group or a cyano(C.sub.1-6)alkyl group, R.sup.3 is a (C.sub.1-6)alkyl group or a halo(C.sub.1-6)alkyl group, R.sup.4 and R.sup.5, which may be the same or different, are hydrogen atoms; cyano groups; (C.sub.1-6)alkyl groups; halo(C.sub.1-6)alkyl groups; (C.sub.3-6)cycloalkyl groups; halo(C.sub.3-6)cycloalkyl groups; (C.sub.3-6)cycloalkyl(C.sub.1-6)alkyl groups; (C.sub.1-6)alkoxy groups; halo(C.sub.1-6)alkoxy groups; (C.sub.1-6)alkylthio groups; halo(C.sub.1-6)alkylthio groups; (C.sub.1-6)alkoxy(C.sub.1-6)alkyl groups; (C.sub.1-6)alkylthio(C.sub.1-6)alkyl groups; (C.sub.2-6)alkenyl groups; halo(C.sub.2-6)alkenyl groups; (C.sub.3-6)cycloalkenyl groups; (C.sub.2-6)alkynyl groups; halo(C.sub.2-6)alkynyl groups; (C.sub.1-6)alkylcarbonyl groups; (C.sub.1-6)alkoxycarbonyl groups; unsubstituted phenyl groups; substituted phenyl groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, formyl group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.2-6)alkenyloxy groups, halo(C.sub.2-6)alkenyloxy groups, (C.sub.2-6)alkynyloxy groups, halo(C.sub.2-6)alkynyloxy groups, (C.sub.1-6)alkylcarbonyl groups, (C.sub.1-6)alkoxycarbonyl groups, di(C.sub.1-6)alkylamino groups, di(C.sub.2-6)alkenylamino groups, di(C.sub.2-6)alkynylamino groups, unsubstituted phenyl(C.sub.1-6)alkyl groups, substituted phenyl(C.sub.1-6)alkyl groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of (C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups and cyano group, unsubstituted phenoxy group, substituted phenoxy groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of (C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups and cyano group, unsubstituted heteroaryloxy groups, substituted heteroaryloxy groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of (C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups and cyano group, unsubstituted benzyloxy group, substituted benzyloxy groups having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of (C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups and cyano group, (C.sub.1-6)alkoxyimino(C.sub.1-6)alkyl groups, (C.sub.1-3)alkylenedioxy groups, and (C.sub.2-6)alkylene groups; unsubstituted phenoxy groups; substituted phenoxy groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkoxyimino(C.sub.1-6)alkyl groups and (C.sub.1-3)alkylenedioxy groups; unsubstituted phenylthio groups; substituted phenylthio groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkoxyimino(C.sub.1-6)alkyl groups and (C.sub.1-3)alkylenedioxy groups; unsubstituted phenyl(C.sub.1-6)alkyl groups; substituted phenyl(C.sub.1-6)alkyl groups having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkoxyimino(C.sub.1-6)alkyl groups and (C.sub.1-3)alkylenedioxy groups; unsubstituted phenyl(C.sub.2-6)alkenyl groups; substituted phenyl(C.sub.2-6)alkenyl groups having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkoxyimino(C.sub.1-6)alkyl groups and (C.sub.1-3)alkylenedioxy groups; unsubstituted phenylcarbonyl groups; substituted phenylcarbonyl groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkoxyimino(C.sub.1-6)alkyl groups and (C.sub.1-3)alkylenedioxy groups; unsubstituted phenoxycarbonyl groups; substituted phenoxycarbonyl groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkoxyimino(C.sub.1-6)alkyl groups and (C.sub.1-3)alkylenedioxy groups; unsubstituted phenoxy(C.sub.1-6)alkyl groups; substituted phenoxy(C.sub.1-6)alkyl groups having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkoxyimino(C.sub.1-6)alkyl groups and (C.sub.1-3)alkylenedioxy groups; unsubstituted phenylthio(C.sub.1-6)alkyl groups; substituted phenylthio(C.sub.1-6)alkyl groups having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkoxyimino(C.sub.1-6)alkyl groups and (C.sub.1-3)alkylenedioxy groups; unsubstituted phenyl(C.sub.1-6)alkylthio groups; substituted phenyl(C.sub.1-6)alkylthio groups having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkoxyimino(C.sub.1-6)alkyl groups and (C.sub.1-3)alkylenedioxy groups; unsubstituted phenyl(C.sub.1-6)alkylcarbonyl groups; substituted phenyl(C.sub.1-6)alkylcarbonyl groups having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkoxyimino(C.sub.1-6)alkyl groups and (C.sub.1-3)alkylenedioxy groups; unsubstituted phenyl(C.sub.1-6)alkoxycarbonyl groups; substituted phenyl(C.sub.1-6)alkoxycarbonyl groups having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkoxyimino(C.sub.1-6)alkyl groups and (C.sub.1-3)alkylenedioxy groups; 5- to 7-membered heterocyclic rings having 1 to 3 heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom; heterocyclic rings having a benzene ring condensed therewith; or heterocyclic rings having a (C.sub.3-6)cycloalkane group condensed therewith; the above heterocyclic rings being able to have one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkoxycarbonyl groups, unsubstituted phenyl group, substituted phenyl groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms and (C.sub.1-6)alkyl groups, phenyl(C.sub.1-6)alkyl groups, pyridyl group, pyrimidyl group and dioxolane group, and Y is an oxygen atom or a sulfur atom.
2. Related Art
EP Laid-Open No. 0498396 and WO93/15046 disclose that N-phenylcarbamate derivatives are useful as agricultural and horticultural fungicides.